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Issue 69, 2014
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Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

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Abstract

The chiral base n-BuLi/(−)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39–48% and ers up to 97 : 3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.

Graphical abstract: Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

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Publication details

The article was received on 16 Jun 2014, accepted on 11 Jul 2014 and first published on 11 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC04576A
Citation: Chem. Commun., 2014,50, 9910-9913
  • Open access: Creative Commons BY license
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    Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

    E. J. Cochrane, D. Leonori, L. A. Hassall and I. Coldham, Chem. Commun., 2014, 50, 9910
    DOI: 10.1039/C4CC04576A

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